My friend of longest standing has been, let us say, rather randy throughout his life. His current status may strike someone as far removed from the White House transition decisions, but I see similarities.

A noted philanderer, he has been benign for the last five years while pursuing a serious romantic relationship with the current love of his life. Yes, there have been others.

He and his girlfriend recently became engaged, even though both are at an age that allows little time to conclude these matters. Men gossip, and so at the possible wedding news, my friends phoned one another to discuss its import. “I’m thrilled,” said a man who, like the rest of us, has enjoyed our friend’s exploits vicariously over the years. “He needs to get married so he can start dating again.”

And that, believe it or not, brought me to an examination of the daunting task President-elect Barack Obama faces in choosing his Cabinet.

While many among us have high expectations that his election signifies a break from our past and will usher in new ideas and new people to Washington, Obama’s early deliberations echo with names from the past. The cronies of Bill Clinton’s era are hovering.

Rahm Emanuel . New Mexico Gov. Bill Richardson . Ex-Clinton chief of staff John Podesta. And even the former First Lady herself, Sen. Hillary Rodham Clinton .

All these familiar Washington insiders’ names keep cropping up — and we were looking to read that rock-star investor Warren Buffett would be spotted leaving Obama’s transition offices after an obligatory interview.

The dilemma Obama faces is similar to that of my roving bachelor friend. He has promised, and more than likely wants, fresh faces. But he also needs the security of continuity.

Washington’s vast bureaucracy, the history of our government, members of Congress with an almost legacy grip on their jobs, special interest groups marauding for help on pet projects – all these create a system that can devour the inexperienced.

This is neither the first time we have been promised change nor the first time we have been disappointed to learn that our expectations of outsiders entering the Beltway are likely to be dashed.

Jimmy Carter ran as an outsider and found himself back on the outside faster than he wanted.

He became a victim of events — most notably double-digit inflation and the humiliation of having U.S. diplomats paraded around in blindfolds by an Iranian mob for 444 days.

But before he became a victim of events, he was a victim of himself, depending heavily on guys he brought to Washington from Georgia, who were ill-equipped for the challenges they didn’t seem to respect.